Lactide copolymers and ring-opened lactide copolymers

ABSTRACT

An article of manufacture. The article of manufacture includes a ring-opened lactide copolymer. The ring-opened lactide copolymer is formed in a process that includes reacting a functionalized lactide monomer with a BPA-derived monomer. The reaction forms a lactide copolymer, which is reacted to form the ring-opened lactide copolymer.

BACKGROUND

Plastics are typically derived from a finite and dwindling supply ofpetrochemicals, resulting in price fluctuations and supply chaininstability. Replacing non-renewable petroleum-based polymers withpolymers derived from renewable resources may be desirable. However,there may be limited alternatives to petroleum-based polymers in certaincontexts. To illustrate, particular plastics performance standards maybe specified by a standards body or by a regulatory agency. In somecases, alternatives to petroleum-based polymers may be limited as aresult of challenges associated with satisfying particular plasticsperformance standards.

SUMMARY

According to an embodiment, an article of manufacture is disclosed. Thearticle of manufacture includes a ring-opened lactide copolymer. Thearticle of manufacture can be a coating, an electrical insulator, afiber-reinforced plastic, or an adhesive. The ring-opened lactidecopolymer can be a component of a resin, such as a thermoset epoxyresin. The ring-opened lactide copolymer can be crosslinked by moietiessuch as epoxies, isocyanates, carbonates, esters, or combinationsthereof. The ring-opened lactide copolymer can be formed by a processthat includes reacting a functionalized lactide monomer with adifunctional epoxide monomer, such as bisphenol A diglycidyl ether.

The foregoing and other objects, features, and advantages of theinvention will be apparent from the following more particulardescriptions of exemplary embodiments of the invention as illustrated inthe accompanying drawings wherein like reference numbers generallyrepresent like parts of exemplary embodiments of the invention.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1A is a chemical reaction diagram illustrating an example of aprocess of forming a first functionalized lactide monomer that isderived from a dimethylidene lactide molecule, according to anembodiment.

FIG. 1B is a chemical reaction diagram illustrating an example of aprocess of utilizing the first functionalized lactide monomer of FIG. 1Ato form a first lactide copolymer.

FIG. 1C is a chemical reaction diagram illustrating an example of aprocess of forming a first ring-opened lactide copolymer from the firstlactide copolymer of FIG. 1B, according to one embodiment.

FIG. 2A is a chemical reaction diagram illustrating an example of aprocess of forming a second functionalized lactide monomer that isderived from a dimethylidene lactide molecule, according to anembodiment.

FIG. 2B is a chemical reaction diagram illustrating an example of aprocess of utilizing the first functionalized lactide monomer of FIG. 2Ato form a second lactide copolymer.

FIG. 2C is a chemical reaction diagram illustrating an example of aprocess of forming a second ring-opened lactide copolymer from thesecond lactide copolymer of FIG. 2B, according to one embodiment.

FIG. 3A is a chemical reaction diagram illustrating an example of aprocess of forming a third functionalized lactide monomer that isderived from a dimethylidene lactide molecule, according to anembodiment.

FIG. 3B is a chemical reaction diagram illustrating an example of aprocess of utilizing the third functionalized lactide monomer of FIG. 3Ato form a second lactide copolymer.

FIG. 3C is a chemical reaction diagram illustrating an example of aprocess of forming a third ring-opened lactide copolymer from the thirdlactide copolymer of FIG. 3B, according to one embodiment.

FIG. 4 is a flow diagram depicting a particular embodiment of a processof utilizing a functionalized lactide monomer derived from adimethylidene lactide molecule to form a lactide copolymer.

FIG. 5 is a flow diagram depicted a particular embodiment of a processof utilizing a functionalized lactide monomer derived from adimethylidene lactide molecule to form a lactide copolymer and utilizingthe lactide copolymer to form a ring-opened lactide copolymer.

DETAILED DESCRIPTION

The present disclosure describes functionalized lactide monomers derivedfrom a dimethylidene lactide molecule, lactide copolymers formed fromthe functionalized lactide monomers, and ring-opened lactide copolymersformed from the lactide copolymers. In the present disclosure, anL-lactide molecule may be utilized to form a dimethylidene lactidemolecule. The exocyclic double bonds on the dimethylidene lactide (DML)molecule can undergo further functionalization to create lactidemonomers with functional groups (also referred to herein as“functionalized lactide monomers”). In some cases, the functionalizedlactide monomers may be polymerized with a bisphenol A (BPA) monomer ora BPA derivative monomer, such as bisphenol A diglycidyl ether (DGEBA),to form lactide copolymers. In other cases, the lactide copolymers mayundergo ring-opening polymerization to form ring-opened lactidecopolymers. While the present disclosure describes functionalization ofDML molecules with epoxide groups and hydroxyl groups for subsequentformation of lactide copolymers, it will be appreciated that the DMLmolecules may be functionalized with alternative and/or additionalgroups. To illustrate, the functionalized lactide monomers of thepresent disclosure may include lactide monomers functionalized withvinyl group(s), amine group(s), anhydride(s), etc., among otheralternatives.

Referring to FIG. 1A, a chemical reaction diagram 100 illustrates anexample of a process of forming a first functionalized lactide monomer102. FIG. 1B is a chemical reaction diagram 110 illustrating that, insome cases, the first functionalized lactide monomer 102 of FIG. 1A maybe utilized to form a first lactide copolymer 112. FIG. 1C is a chemicalreaction diagram 120 illustrating that, in some cases, the first lactidecopolymer 112 of FIG. 1B may be utilized to form a first ring-openedlactide copolymer 122.

The first two chemical reactions depicted in FIG. 1A illustrate theformation of a dimethylidene lactide molecule from an L-lactidemolecule. In a particular embodiment, formation of the dimethylidenelactide molecule may include radical bromination (depicted as Br₂, hv inFIG. 1A) in the presence to carbon tetrachloride (CCl₄). Subsequently,FIG. 1A illustrates that elimination with triethylamine (NEt₃) in asolvent such as dichloromethane (DCM) results in the formation of thedimethylidene lactide (DML) molecule.

As a prophetic example, the DML molecule may be formed byphotobromination of the L-lactide molecule in a carbon tetrachloride(CCl₄) solution using a mercury vapor lamp (e.g., a H-100A-38-4 mercuryvapor lamp from General Electric, Inc.). The dibrominated intermediatemolecule may be dehydrobrominated by reaction with triethylamine (NEt₃)in a carefully dried ether. The resulting crude DML molecule may then bepurified according to a purification procedure known to one of ordinaryskill in the art.

The third chemical reaction depicted in FIG. 1A illustrates that thefirst functionalized lactide monomer 102 may be synthesized from the DMLmolecule. In a particular embodiment, the third chemical reaction ofFIG. 1A may include chemically reacting 2-oxiranemethanethiol via atriethylamine-catalyzed Michael addition with DML to form the firstfunctionalized lactide monomer 102, representing an example of abisthioepoxide functionalized lactide molecule. As a prophetic example,to a solution of 2-Oxiranemethanethiol (2.1 eqiuv.), and triethylamine(0.3 equiv.) in anhydrous acetonitrile, may be added a solution of DML(1.0 equiv.) in anhydrous acetonitrile, dropwise at 0° C., under aninert atmosphere. The reaction mixture may be stirred for 1.5 hours at0° C., and then concentrated by about 80% in vacuo. The concentratedsolution may be dissolved in ethyl acetate and washed with 0.1 M HCl(×3), dried over MgSO₄, filtered, and the solvents removed in vacuo. Theresulting solid may be purified by column chromatography orrecrystallization.

Referring to FIG. 1B, a chemical reaction diagram 110 illustrates thatthe first functionalized lactide monomer 102 of FIG. 1A may be used toform a first lactide copolymer 112, representing a first example of alactide-BPA copolymer. In a particular embodiment, the firstfunctionalized lactide monomer 102 may be reacted with BPA under basicconditions (depicted as “B⁻” in FIG. 1B) to form the first lactidecopolymer 112. In some cases, the first lactide copolymer 112 of FIG. 1Bmay be used in resins. In other cases, the first lactide copolymer 112of FIG. 1B may be reacted further to make a cross-linked poly(lacticacid) network, as illustrated and described further herein with respectto FIG. 1C.

Referring to FIG. 1C, a chemical reaction diagram 120 illustrates anexample of a process of forming a first ring-opened lactide copolymer122 from the first lactide copolymer 112 of FIG. 1B. In the example ofFIG. 1C, synthesis of the first ring-opened lactide copolymer 122 mayinclude reacting the first lactide copolymer 112 with a tin(II)octanoate material (depicted as “Sn(OC₈H¹⁷)₂” in FIG. 1C) underring-opening polymerization conditions. The first ring-opened lactidecopolymer 122 of FIG. 1C represents a first example of a cross-linkedpolymer that may be utilized as a renewable alternative for epoxythermoset resins, such as coatings, electrical insulators,fiber-reinforced plastics, and structural adhesives, among otheralternatives. In some cases, formulation of such a renewable thermosetmaterial may take place before the cross-linking reaction depicted inFIG. 1C in order to incorporate additives, plasticizers, fillers, orcombinations thereof (among other alternatives). Further, it will beappreciated that the first lactide copolymer 112 of FIG. 1B alsoincludes free hydroxyl groups that can also be cross-linked further withother epoxy groups, isocyanates, carbonates, esters, etc. to fromalternative thermoset materials.

Thus, FIGS. 1A-1C illustrate an example of a process of forming afunctionalized lactide monomer and utilizing the functionalized lactidemonomer to form a lactide copolymer (e.g., a BPA-lactide copolymer) or aring-opened lactide copolymer. While not shown in the example of FIGS.1A-1C, the lactide copolymers and/or ring-opened lactide copolymers maybe utilized to form various articles of manufacture. As an example, theBPA-lactide copolymer depicted in FIG. 1B (prior to ring-openingpolymerization) may be used in resins. As another example, thering-opened BPA-lactide copolymer of FIG. 1C may be utilized as arenewable alternative for epoxy thermoset resins, such as coatings,electrical insulators, fiber-reinforced plastics, and structuraladhesives, among other alternatives.

Referring to FIG. 2A, a chemical reaction diagram 200 illustrates anexample of a process of forming a second functionalized lactide monomer202. FIG. 2B is a chemical reaction diagram 210 illustrating that, insome cases, the first functionalized lactide monomer 202 of FIG. 2A maybe utilized to form a second lactide copolymer 212. FIG. 2C is achemical reaction diagram 220 illustrating that, in some cases, thesecond lactide copolymer 212 of FIG. 2B may be utilized to form a secondring-opened lactide copolymer 222.

The first two chemical reactions depicted in FIG. 2A illustrate theformation of a dimethylidene lactide molecule from an L-lactidemolecule. The process of forming the dimethylidene lactide molecule maybe similar to the process previously described herein with respect toFIG. 1A.

The second chemical reaction depicted in FIG. 2A illustrates that thesecond functionalized lactide monomer 202 may be synthesized from theDML molecule. In a particular embodiment, the second chemical reactionof FIG. 2A may include chemically reacting the DML molecule underhydroboration conditions to form the second functionalized lactidemonomer 202, representing an example of a diol functionalized lactidemolecule. While not shown in the example of FIG. 2A, in some cases, aprotecting group may be utilized for the hydroxyl groups of the secondfunctionalized lactide monomer 202. As a prophetic example, 9-BBN (0.5 Min THF, 2.1 equiv.) may be added dropwise over 30 min to a stirred andcooled (0° C.) solution of DML (1.0 equiv.) in THF (125 mL). The icebath may be removed, and stirring may continue for 12 hours. The mixturemay be cooled to 0° C. and quenched by dropwise addition of MeOH.Aqueous NaOH (2 M, >1.5 equiv.) and 30% H₂O₂ (>10.0 equiv.) may bepoured into the stirred mixture. Stirring may be continued for 2 hours,and the mixture may be extracted with Et₂O. The combined organicextracts may be washed with brine, dried over Na₂SO₄, and the solventmay be removed in vacuo. The crude product may be purified throughcolumn chromatography.

Referring to FIG. 2B, a chemical reaction diagram 210 illustrates thatthe second functionalized lactide monomer 202 of FIG. 2A may be used toform a second lactide copolymer 212, representing a first example of alactide-DGEBA copolymer. While FIG. 2A illustrates a particularembodiment in which the BPA derivative includes DGEBA, it will beappreciated that other di-functional epoxides may also be utilized. Asan illustrative, non-limiting example, an alternative bis-epoxy materialmay include a cycloaliphatic diepoxide, such as ERL-4221(3,4-Epoxycyclohexanemethyl 3,4-epoxycyclohexanecarboxylate), amongother alternatives. In a particular embodiment, the secondfunctionalized lactide monomer 202 may be reacted with DGEBA under basicconditions (depicted as “B⁻” in FIG. 2B) to form the second lactidecopolymer 212. In some cases, the second lactide copolymer 212 of FIG.2B may be used in resins. In other cases, the second lactide copolymer212 of FIG. 2B may be reacted further to make a cross-linked poly(lacticacid) network, as illustrated and described further herein with respectto FIG. 2C.

Referring to FIG. 2C, a chemical reaction diagram 220 illustrates anexample of a process of forming a second ring-opened lactide copolymer222 from the second lactide copolymer 212 of FIG. 2B. In the example ofFIG. 2C, synthesis of the second ring-opened lactide copolymer 222 mayinclude reacting the first lactide copolymer 212 with a tin(II)octanoate material (depicted as “Sn(OC₈H₁₇)₂” in FIG. 2C) underring-opening polymerization conditions. The second ring-opened lactidecopolymer 222 of FIG. 2C represents a first example of a cross-linkedpolymer that may be utilized as a renewable alternative for epoxythermoset resins, such as coatings, electrical insulators,fiber-reinforced plastics, and structural adhesives, among otheralternatives. In some cases, formulation of such a renewable thermosetmaterial may take place before the cross-linking reaction depicted inFIG. 2C in order to incorporate additives, plasticizers, fillers, orcombinations thereof (among other alternatives). Further, it will beappreciated that the second lactide copolymer 212 of FIG. 2B alsoincludes free hydroxyl groups that can also be cross-linked further withother epoxy groups, isocyanates, carbonates, esters, etc. to fromalternative thermoset materials.

Thus, FIGS. 2A-2C illustrate an example of a process of forming afunctionalized lactide monomer and utilizing the functionalized lactidemonomer to form a lactide copolymer (e.g., a DGEBA-lactide copolymer) ora ring-opened lactide copolymer. While not shown in the example of FIGS.2A-2C, the lactide copolymers and/or ring-opened lactide copolymers maybe utilized to form various articles of manufacture. As an example, theDGEBA-lactide copolymer depicted in FIG. 2B (prior to ring-openingpolymerization) may be used in resins. As another example, thering-opened DGEBA-lactide copolymer of FIG. 2C may be utilized as arenewable alternative for epoxy thermoset resins, such as coatings,electrical insulators, fiber-reinforced plastics, and structuraladhesives, among other alternatives.

Referring to FIG. 3A, a chemical reaction diagram 300 illustrates anexample of a process of forming a third functionalized lactide monomer302. FIG. 3B is a chemical reaction diagram 310 illustrating that, insome cases, the third functionalized lactide monomer 302 of FIG. 3A maybe utilized to form a third lactide copolymer 312. FIG. 3C is a chemicalreaction diagram 320 illustrating that, in some cases, the third lactidecopolymer 312 of FIG. 3B may be utilized to form a third ring-openedlactide copolymer 322.

The first two chemical reactions depicted in FIG. 3A illustrate theformation of a dimethylidene lactide molecule from an L-lactidemolecule. The process of forming the dimethylidene lactide molecule maybe similar to the process previously described herein with respect toFIG. 1A. The third chemical reaction depicted in FIG. 3A illustratesthat the third functionalized lactide monomer 302 may be synthesizedfrom the DML molecule. In a particular embodiment, the third chemicalreaction of FIG. 3A may include chemically reactingmeta-chloroperbenzoic acid (MCPBA) with DML to form the thirdfunctionalized lactide monomer 302, representing an example of abisepoxide-functionalized lactide molecule. As a prophetic example,MCPBA (meta-chloroperbenzoic acid, >2.0 equiv) and DML (1.0 equiv.) maybe dissolved in dichloromethane. The reaction mixture may be heated withstirring, under reflux, for 24 hours. After completion, the mixture maybe washed with a saturated solution of sodium bicarbonate and 10%aqueous sodium bisulfite. Subsequently, the organic phase may be driedover magnesium sulfate, filtered, and the solvents may be removed invacuo. The resulting solid may be purified by recrystallization orcolumn chromatography.

Referring to FIG. 3B, a chemical reaction diagram 310 illustrates thatthe third functionalized lactide monomer 302 of FIG. 3A may be used toform a third lactide copolymer 312, representing a second example of alactide-BPA copolymer (that is different from the lactide-BPA copolymerdepicted in FIG. 1B). In a particular embodiment, the thirdfunctionalized lactide monomer 302 may be reacted with BPA under basicconditions (depicted as “B⁻” in FIG. 3B) to form the third lactidecopolymer 312. In some cases, the third lactide copolymer 312 of FIG. 3Bmay be used in resins. In other cases, the third lactide copolymer 312of FIG. 3B may be reacted further to make a cross-linked poly(lacticacid) network, as illustrated and described further herein with respectto FIG. 3C.

Referring to FIG. 3C, a chemical reaction diagram 320 illustrates anexample of a process of forming a third ring-opened lactide copolymer322 from the third lactide copolymer 312 of FIG. 3B. In the example ofFIG. 3C, synthesis of the third ring-opened lactide copolymer 322 mayinclude reacting the third lactide copolymer 312 with a tin(II)octanoate material (depicted as “Sn(OC₈H₁₇)₂” in FIG. 3C) underring-opening polymerization conditions. The third ring-opened lactidecopolymer 322 of FIG. 3C represents a third example of a cross-linkedpolymer that may be utilized as a renewable alternative for epoxythermoset resins, such as coatings, electrical insulators,fiber-reinforced plastics, and structural adhesives, among otheralternatives. In some cases, formulation of such a renewable thermosetmaterial may take place before the cross-linking reaction depicted inFIG. 3C in order to incorporate additives, plasticizers, fillers, orcombinations thereof (among other alternatives). Further, it will beappreciated that the third lactide copolymer 312 of FIG. 3B alsoincludes free hydroxyl groups that can also be cross-linked further withother epoxy groups, isocyanates, carbonates, esters, etc. to fromalternative thermoset materials.

Thus, FIGS. 3A-3C illustrate an example of a process of forming afunctionalized lactide monomer and utilizing the functionalized lactidemonomer to form a lactide copolymer (e.g., a BPA-lactide copolymer) or aring-opened lactide copolymer. While not shown in the example of FIGS.3A-3C, the lactide copolymers and/or ring-opened lactide copolymers maybe utilized to form various articles of manufacture. As an example, theBPA-lactide copolymer depicted in FIG. 3B (prior to ring-openingpolymerization) may be used in resins. As another example, thering-opened BPA-lactide copolymer of FIG. 3C may be utilized as arenewable alternative for epoxy thermoset resins, such as coatings,electrical insulators, fiber-reinforced plastics, and structuraladhesives, among other alternatives.

Referring to FIG. 4, a flow diagram illustrates a particular embodimentof a process 400 of utilizing a functionalized lactide monomer derivedfrom a dimethylidene lactide molecule to form a lactide copolymer. Whilenot shown in the example of FIG. 4, the process 400 may further includeforming an article of manufacture from the lactide copolymer (e.g., aresin material).

The process 400 includes forming a dimethylidene lactide molecule froman L-lactide molecule, at 402. For example, referring to FIG. 1A, thedimethylidene lactide molecule may be formed from the L-lactide moleculeby radical bromination of the L-lactide molecule, followed byelimination with triethylamine (NEt₃).

The process 400 includes forming a functionalized lactide monomer fromthe dimethylidene lactide molecule, at 404. For example, referring toFIG. 1A, the dimethylidene lactide molecule may be utilized to form thefirst functionalized lactide monomer 102, representing an example of abisthioepoxide-functionalized lactide monomer. As another example,referring to FIG. 2A, the dimethylidene lactide molecule may be utilizedto form the second functionalized lactide monomer 202, representing anexample of a diol-functionalized lactide monomer. As another example,referring to FIG. 3A, the dimethylidene lactide molecule may be utilizedto form the third functionalized lactide monomer 302, representing anexample of a bisepoxide-functionalized lactide monomer.

The process 400 includes forming a mixture that includes thefunctionalized lactide monomer and a BPA monomer or a BPA-derivedmonomer, at 406. The process 400 also includes polymerizing the mixtureto form a lactide copolymer, at 408.

As an example, referring to FIG. 1B, the first functionalized lactidemonomer 102 of FIG. 1A may be reacted with BPA under basic conditions(depicted as “B⁻” in FIG. 1B) to form the first lactide copolymer 112.In some cases, the first lactide copolymer 112 of FIG. 1B may be used toform an article of manufacture that includes a resin material. In othercases, as illustrated and further described herein with respect to FIG.5, the first lactide copolymer 112 of FIG. 1B may be used to form thering-opened lactide copolymer 122 of FIG. 1C.

As another example, referring to FIG. 2B, the second functionalizedlactide monomer 202 of FIG. 2A may be reacted with DGEBA under basicconditions (depicted as “B⁻” in FIG. 2B) to form the second lactidecopolymer 212. In some cases, the second lactide copolymer 212 of FIG.2B may be used to form an article of manufacture that includes a resinmaterial. In other cases, as illustrated and further described hereinwith respect to FIG. 5, the second lactide copolymer 212 of FIG. 2B maybe used to form the ring-opened lactide copolymer 222 of FIG. 2C.

As yet another example, referring to FIG. 3B, the third functionalizedlactide monomer 302 of FIG. 3A may be reacted with BPA under basicconditions (depicted as “B⁻” in FIG. 3B) to form the third lactidecopolymer 312. In some cases, the third lactide copolymer 312 of FIG. 3Bmay be used to form an article of manufacture that includes a resinmaterial. In other cases, as illustrated and further described hereinwith respect to FIG. 5, the third lactide copolymer 312 of FIG. 3B maybe used to form the ring-opened lactide copolymer 322 of FIG. 3C.

Thus, FIG. 4 illustrates an example of a process of utilizing afunctionalized lactide monomer derived from a dimethylidene lactidemolecule to form a lactide copolymer. As illustrated and furtherdescribed herein with respect to FIG. 5, in some cases, the lactidecopolymer may be subsequently utilized to form a ring-opened lactidecopolymer.

Referring to FIG. 5, a flow diagram illustrates a particular embodimentof a process 500 of utilizing the lactide copolymer formed according tothe process 400 depicted in FIG. 4 to form a ring-opened lactidecopolymer. In the particular embodiment depicted in FIG. 5, the process500 further includes forming an article of manufacture from thering-opened lactide copolymer.

The process 500 includes forming a functionalized lactide monomer from adimethylidene lactide molecule (that is formed from a renewableL-lactide molecule), at 502.

For example, referring to FIG. 1A, the dimethylidene lactide moleculemay be utilized to form the first functionalized lactide monomer 102,representing an example of a bisthioepoxide-functionalized lactidemonomer. As another example, referring to FIG. 2A, the dimethylidenelactide molecule may be utilized to form the second functionalizedlactide monomer 202, representing an example of a diol-functionalizedlactide monomer. As another example, referring to FIG. 3A, thedimethylidene lactide molecule may be utilized to form the thirdfunctionalized lactide monomer 302, representing an example of abisepoxide-functionalized lactide monomer.

The process 500 includes forming a mixture that includes thefunctionalized lactide monomer and a BPA monomer or a BPA-derivedmonomer, at 504. The process 500 also includes polymerizing the mixtureto form a lactide copolymer, at 506.

As an example, referring to FIG. 1B, the first functionalized lactidemonomer 102 of FIG. 1A may be reacted with BPA under basic conditions(depicted as “B⁻” in FIG. 1B) to form the first lactide copolymer 112.As another example, referring to FIG. 2B, the second functionalizedlactide monomer 202 of FIG. 2A may be reacted with DGEBA under basicconditions (depicted as “B⁻” in FIG. 2B) to form the second lactidecopolymer 212. As yet another example, referring to FIG. 3B, the thirdfunctionalized lactide monomer 302 of FIG. 3A may be reacted with BPAunder basic conditions (depicted as “B⁻” in FIG. 3B) to form the thirdlactide copolymer 312.

The process 500 further includes forming a ring-opened lactide copolymerfrom the lactide copolymer, at 508. As an example, referring to FIG. 1C,the first lactide copolymer 112 may be utilized to form the firstring-opened lactide copolymer 122. As another example, referring to FIG.2C, the second lactide copolymer 212 of FIG. 2B may be utilized to formthe second ring-opened lactide copolymer 222. As yet another example,the third lactide copolymer 312 of FIG. 3B may be utilized to form thethird ring-opened lactide copolymer 322.

In the particular embodiment depicted in FIG. 5, the process 500 furtherincludes forming an article of manufacture that includes the ring-openedlactide copolymer, at 510. For example, the article of manufacture mayinclude a renewable alternative for epoxy thermoset resins, such ascoatings, electrical insulators, fiber-reinforced plastics, andstructural adhesives, among other alternatives.

Thus, FIG. 5 illustrates an example of a process of utilizing thelactide copolymer formed according to the process described herein withrespect to FIG. 4 to form a ring-opened lactide copolymer. FIG. 5further illustrates that, in some cases, the ring-opened lactidecopolymers of the present disclosure may be utilized to form articles ofmanufacture that represent renewable alternatives to some existingpetroleum-derived materials.

It will be understood from the foregoing description that modificationsand changes may be made in various embodiments of the present inventionwithout departing from its true spirit. The descriptions in thisspecification are for purposes of illustration only and are not to beconstrued in a limiting sense. The scope of the present invention islimited only by the language of the following claims.

What is claimed is:
 1. An article of manufacture, comprising aring-opened lactide copolymer.
 2. The article of manufacture of claim 1,wherein the ring-opened lactide copolymer has the following structure:


3. The article of manufacture of claim 1, wherein the ring-openedlactide copolymer has the following structure:


4. The article of manufacture of claim 4, wherein the ring-openedlactide copolymer is a component of a resin.
 5. The article ofmanufacture of claim 4, wherein the resin is a thermoset epoxy resin. 6.The article of manufacture of claim 1, wherein the article ofmanufacture is selected from the group consisting of: a coating, anelectrical insulator, a fiber-reinforced plastic, and an adhesive. 7.The article of manufacture of claim 1, wherein the ring-opened lactidecopolymer is cross-linked by crosslinking moieties.
 8. The article ofmanufacture of claim 7, wherein the cros slinking moieties are selectedfrom the group consisting of epoxies, isocyanates, carbonates, esters,and combinations thereof.
 9. The article of manufacture of claim 1,wherein the ring-opened lactide copolymer is formed in a process thatincludes a reaction to form a lactide copolymer.
 10. The article ofmanufacture of claim 9, wherein the reaction is a polymerizationreaction between a functionalized lactide monomer and a difunctionalepoxide monomer.
 11. The article of manufacture of claim 10, wherein thefunctionalized lactide monomer is selected from the group consisting of:


12. The article of manufacture of claim 10, wherein the difunctionalepoxide monomer is bisphenol A diglycidyl ether.